2-(4-Nitro-benzyl-idene)malononitrile.

In the title compound, C(10)H(5)N(3)O(2), the benzyl-idene-malono-nitrile unit is nearly planar, with a maximum deviation of 0.129 (2) Å for a terminal N atom; the nitro group is approximately coplanar with the benzene ring [dihedral angle = 8.8 (3)°]. An intra-molecular C-H⋯N hydrogen bond stabilizes the mol-ecular conformation.

Related literature

For the preparation of the title compound, see: Baheti et al. (2011 ▶). For the spectroscopy and applications of benzyl­idenemalononitrile derivatives, see: Cao et al. (2010 ▶); Ding & Zhao (2010 ▶); Elinson et al. (2010 ▶); Herbivo et al. (2010 ▶); Shigemitsu et al. (2011 ▶); Ye et al. (2010 ▶). For related structures, see: El Brahmi et al. (2011 ▶); Karthikeyan et al. (2011 ▶); Mehdi et al. (2010 ▶); Ouzidan et al. (2011 ▶); Raza et al. (2010 ▶).

Experimental

Crystal data

C10H5N3O2

M = 199.17

Orthorhombic,

a = 19.5557 (9) Å

b = 3.8732 (2) Å

c = 11.9823 (5) Å

V = 907.58 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.89 mm−1

T = 297 K

0.76 × 0.60 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.674, T max = 1.000

3111 measured reflections

1517 independent reflections

1420 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.06

1517 reflections

136 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 582 Friedel pairs

Flack parameter: −0.2 (2)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008896/xu5449sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008896/xu5449Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008896/xu5449Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H5N3O2	F(000) = 408
Mr = 199.17	Dx = 1.458 Mg m−3
Orthorhombic, Pna21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 2320 reflections
a = 19.5557 (9) Å	θ = 3.7–71.5°
b = 3.8732 (2) Å	µ = 0.89 mm−1
c = 11.9823 (5) Å	T = 297 K
V = 907.58 (7) Å3	Parallelepiped, colorless
Z = 4	0.76 × 0.60 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	1517 independent reflections
Radiation source: fine-focus sealed tube	1420 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 71.7°, θmin = 4.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −24→15
Tmin = 0.674, Tmax = 1.000	k = −4→3
3111 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.0168P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1517 reflections	Δρmax = 0.13 e Å−3
136 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 582 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.2 (2)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.19540 (9)	1.1888 (6)	−0.10487 (14)	0.0798 (6)
O2	0.17348 (9)	1.4626 (5)	0.04698 (17)	0.0790 (6)
N1	0.21000 (8)	1.2840 (4)	−0.01057 (15)	0.0530 (4)
N2	0.61988 (11)	0.5187 (6)	0.25478 (17)	0.0672 (5)
N3	0.53572 (10)	0.5513 (7)	−0.07973 (17)	0.0743 (6)
C1	0.38494 (10)	0.9176 (5)	0.00650 (14)	0.0445 (4)
H1A	0.4165	0.8120	−0.0404	0.053*
C2	0.32231 (10)	1.0153 (5)	−0.03437 (15)	0.0449 (4)
H2A	0.3110	0.9738	−0.1086	0.054*
C3	0.27635 (9)	1.1752 (5)	0.03563 (14)	0.0405 (4)
C4	0.29078 (10)	1.2411 (5)	0.14638 (16)	0.0471 (5)
H4A	0.2591	1.3505	0.1922	0.056*
C5	0.35351 (10)	1.1396 (5)	0.18681 (15)	0.0447 (4)
H5A	0.3641	1.1811	0.2613	0.054*
C6	0.40158 (9)	0.9766 (4)	0.11918 (14)	0.0387 (4)
C7	0.46578 (10)	0.8685 (5)	0.17120 (14)	0.0415 (4)
H7A	0.4690	0.9154	0.2471	0.050*
C8	0.52069 (10)	0.7129 (4)	0.12720 (15)	0.0408 (4)
C9	0.57642 (11)	0.6105 (5)	0.19838 (16)	0.0478 (5)
C10	0.52915 (9)	0.6242 (6)	0.01095 (17)	0.0489 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0629 (11)	0.1147 (15)	0.0617 (10)	0.0171 (10)	−0.0179 (8)	−0.0051 (10)
O2	0.0585 (9)	0.0933 (14)	0.0852 (13)	0.0283 (9)	0.0017 (9)	−0.0088 (10)
N1	0.0435 (9)	0.0578 (10)	0.0577 (12)	0.0029 (7)	0.0036 (8)	0.0085 (9)
N2	0.0659 (12)	0.0835 (14)	0.0521 (10)	0.0141 (11)	−0.0141 (10)	0.0016 (9)
N3	0.0567 (11)	0.1197 (18)	0.0464 (10)	0.0190 (11)	−0.0019 (9)	−0.0203 (11)
C1	0.0467 (9)	0.0544 (11)	0.0324 (8)	0.0064 (8)	0.0011 (7)	−0.0025 (8)
C2	0.0470 (9)	0.0543 (11)	0.0334 (8)	0.0003 (8)	−0.0011 (8)	−0.0006 (8)
C3	0.0391 (8)	0.0424 (9)	0.0399 (10)	−0.0019 (7)	0.0009 (7)	0.0045 (7)
C4	0.0480 (10)	0.0506 (11)	0.0426 (10)	0.0023 (9)	0.0106 (8)	−0.0029 (9)
C5	0.0501 (10)	0.0529 (11)	0.0312 (8)	−0.0032 (8)	0.0027 (8)	−0.0009 (8)
C6	0.0447 (9)	0.0394 (9)	0.0321 (8)	−0.0029 (7)	0.0016 (7)	0.0030 (7)
C7	0.0515 (10)	0.0439 (11)	0.0290 (7)	−0.0038 (8)	−0.0023 (7)	0.0013 (7)
C8	0.0447 (9)	0.0407 (9)	0.0370 (9)	−0.0041 (8)	−0.0039 (7)	0.0024 (8)
C9	0.0502 (10)	0.0520 (11)	0.0413 (10)	0.0009 (9)	−0.0029 (9)	0.0011 (9)
C10	0.0401 (9)	0.0618 (12)	0.0449 (10)	0.0041 (8)	−0.0009 (8)	−0.0037 (9)

O1—N1	1.222 (2)	C3—C4	1.381 (3)
O2—N1	1.210 (2)	C4—C5	1.376 (3)
N1—C3	1.472 (2)	C4—H4A	0.9300
N2—C9	1.143 (3)	C5—C6	1.393 (3)
N3—C10	1.130 (3)	C5—H5A	0.9300
C1—C2	1.372 (3)	C6—C7	1.463 (3)
C1—C6	1.407 (2)	C7—C8	1.339 (3)
C1—H1A	0.9300	C7—H7A	0.9300
C2—C3	1.377 (3)	C8—C10	1.444 (3)
C2—H2A	0.9300	C8—C9	1.440 (3)
O2—N1—O1	124.15 (19)	C4—C5—C6	121.76 (17)
O2—N1—C3	118.00 (17)	C4—C5—H5A	119.1
O1—N1—C3	117.85 (17)	C6—C5—H5A	119.1
C2—C1—C6	120.27 (17)	C5—C6—C1	118.41 (17)
C2—C1—H1A	119.9	C5—C6—C7	117.46 (17)
C6—C1—H1A	119.9	C1—C6—C7	124.11 (16)
C3—C2—C1	119.29 (17)	C8—C7—C6	130.47 (17)
C3—C2—H2A	120.4	C8—C7—H7A	114.8
C1—C2—H2A	120.4	C6—C7—H7A	114.8
C2—C3—C4	122.37 (17)	C7—C8—C10	125.34 (17)
C2—C3—N1	118.37 (15)	C7—C8—C9	119.85 (17)
C4—C3—N1	119.25 (16)	C10—C8—C9	114.78 (16)
C5—C4—C3	117.89 (18)	N2—C9—C8	177.8 (2)
C5—C4—H4A	121.1	N3—C10—C8	179.3 (3)
C3—C4—H4A	121.1
C6—C1—C2—C3	0.8 (3)	C3—C4—C5—C6	0.2 (3)
C1—C2—C3—C4	−0.2 (3)	C4—C5—C6—C1	0.4 (3)
C1—C2—C3—N1	178.79 (16)	C4—C5—C6—C7	−177.94 (17)
O2—N1—C3—C2	−170.72 (19)	C2—C1—C6—C5	−0.9 (3)
O1—N1—C3—C2	9.0 (3)	C2—C1—C6—C7	177.29 (17)
O2—N1—C3—C4	8.3 (3)	C5—C6—C7—C8	−179.0 (2)
O1—N1—C3—C4	−172.0 (2)	C1—C6—C7—C8	2.8 (3)
C2—C3—C4—C5	−0.3 (3)	C6—C7—C8—C10	2.3 (3)
N1—C3—C4—C5	−179.30 (17)	C6—C7—C8—C9	−175.70 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N3	0.93	2.58	3.431 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N3	0.93	2.58	3.431 (3)	152